2-Aminosubstituted-5-methylene-thiazole and 3-aminosubstituted-1 methylene-2,4-thiazaspiro[5.4]decane herbicides

ABSTRACT

Compounds of the following formula have herbicidal activity: ##STR1## wherein X and Y are hydrogen or halo; R 2  and R 3  are alkyl or are joined to form --CH 2  -- n , n=2 through 7; R is hydrogen, haloacetyl, alkyl, alkoxyalkyl or N-alkylcarbamoyl and R 1  is alkyl, alkenyl, alkynyl, cycloalkyl, polycycloalkyl, alkoxy-alkyl, cyanoalkyl or cyanoalkenyl; with the proviso that when R and R 1  are both alkyl, each contains at least 3 carbon atoms.

BACKGROUND OF THE INVENTION

Azerbaev et al. disclose2-benzylamino-4,4-dialkyl-5-methylene-1,3-thiazolines in Chem. Abstr.79:66237 v (1973).

Eloy et al disclose 2-alkylamino-5-methylene-thiazoles in Chem. Abstr.81:13439x (1974).

SUMMARY OF THE INVENTION

The present invention relates to novel herbicidal compounds,compositions thereof and methods of their use. The present invention isbased on the surprising observation that compounds of the formula (I)have a favorable herbicidal spectrum against weeds in post-emergentapplications.

DESCRIPTION OF THE INVENTION

The present invention relates to compounds of the formula I: ##STR2##wherein X and Y are individually hydrogen or halogen;

R² and R³ are individually alkyl of 1 to 3 carbon atoms or R² and R³ arejoined to form a cycloalkyl group of 3 to 8 carbon atoms;

R is hydrogen, haloacetyl, N-alkyl-carbamoyl of 2 to 10 carbon atoms,alkyl of 1 to 4 carbon atoms or alkoxyalkyl of 2 to 20 carbon atoms; and

R¹ is alkyl of 1 to 20 carbon atoms, alkenyl or alkynyl of 3 to 20carbon atoms, cycloalkyl or polycycloalkyl of 5 to 12 carbon atoms,alkoxyalkyl of 2 to 20 carbon atoms, cyanoalkyl or cyanoalkenyl of 3 to20 carbon atoms; with the proviso that when R and R¹ are both alkylgroups as defined above, R and R¹ each contain at least 3 carbon atoms.

Representative R² and R³ groups are methyl, ethyl, propyl or R² and R³are joined to form a cyclopentyl, cyclohexyl or cycloheptyl group.Preferably, R² and R³ are joined to form a cyclohexyl group.

Representative R groups are hydrogen, methyl, ethyl, n-propyl, i-propyl,n-butyl, N-methyl carbamoyl, ethoxyethyl, methoxymethyl, chloroacetyl,bromoacetyl. Preferably R is hydrogen or N-methylcarbamoyl. Mostpreferably, R is hydrogen.

Representative R¹ groups are methyl, ethyl, n-propyl, t-butyl,sec-butyl, n-butyl, i-butyl, n-hexyl, n-octyl, 3-pentyl, n-pentyl,allyl, butenyl, propynyl, cyclopentyl, cyclohexyl, cyclohexylmethyl,1-acetylenyl-cyclohex-1-yl, exonorborn-2-ane, 2-phenylethyl,p-chlorobenzyl, 4-phenylbutyl, 2-methoxyethyl, 3-methoxyprop-2-yl,ethoxyethyl, 2,2-dicyanoethylene and cyanoethyl. Preferably, R¹ is alkylof 1 to 20 carbon atoms. Most preferably R¹ is alkyl of 1 to 6 carbonatoms.

The compounds of the invention may be made according to the followingscheme: ##STR3##

Reaction (1) is a conventional condensation and may be performed byreacting substantially equimolar portions of the amino propargylcompound (II) with the thiocyano compound (III) to form the cyclicintermediate (IV). The reaction may be conducted in a suitable inertsolvent at 10° C. to 100° C., preferably at about 20° C.-30° C.

Reaction (2) is a conventional addition reaction which may be performedby reacting substantially equimolar amounts of the cyclic compound (IV)with the chloro compound in an inert diluent, preferably in presence ofan organic base, such as, triethylamine, to serve as a scavenger for theevolved hydrogen chloride. The reaction may be carried out at roomtemperature.

The preferred method for making intermediate (IA) is according toreactions (1a) and (1b): ##STR4##

Reaction (1a) may be conducted in an inert organic diluent, preferablywith water as a co-solvent. An organic base, such as a trialkylamine,may be added to scavenge the evolved hydrogen chloride. The reaction isexothermic and the mixture may be cooled to prevent boiling the solvent.The reaction is preferably carried out at room temperature employing aslight molar excess of thiophosgene (IIIA).

Reaction (1b) may be conducted with substantially equimolar amounts of(IIA) and amine (IIIB) in an inert organic diluent. The exothermicreaction may be conducted at 0°-100° C., preferably at 20°-40° C. If Ris hydrogen, product (IA) from reaction (1b) can be further treated asin reaction (2a).

For compounds wherein R is N-methylcarbamoyl, reaction (2a) may be used.It is conducted in an inert solvent at room temperature in the presenceof a base, such as triethylamine.

For compounds wherein X and Y are halogens, reaction (3) may be used.The mono- and dichloro compounds (IC) and (ID) are formed as a mixtureby bubbling gaseous chlorine through a solution of (IA).

UTILITY

The compounds of the present invention are herbicidal in both pre- andpost-emergent applications. For pre-emergent control of undesirablevegetation, the herbicidal compounds will be applied in herbicidallyeffective amounts to the locus or growth medium of the vegetation, e.g.,soil infested with seeds and/or seedlings of such vegetation. Suchapplication will inhibit the growth of or kill the seeds, germinatingseeds and seedlings. For post-emergent applications, the herbicidalcompounds will be applied directly to the foliage and other plant parts.Generally, the herbicidal compounds of the invention are effectiveagainst weed grasses as well as broad-leaved weeds. Some may beselective with respect to the type of application and/or type of weed.

The compounds of the present invention can be used alone as herbicides.However, it is generally desirable to apply the compounds in herbicidalcompositions comprising one or more of the herbicidal compoundsintimately admixed with a biologically inert carrier. The carrier may bea liquid diluent or a solid, e.g., in the form of dust powder orgranules. In the herbicidal composition, the active herbicidal compoundscan be from about 0.01 to 95% by weight of the entire composition.

Suitable liquid diluent carriers include water and organic solvents,e.g., hydrocarbons such as benzene, toluene, kerosene, diesel oil, fueloil, and petroleum naphtha. Suitable solid carriers are natural clayssuch as kaolinite, atalpulgite and montmorillonite. In addition, talcs,pyrophillite, diatomaceous silica, synthetic fine silicas, calciumaluminosilicate and tricalcium phosphate are suitable carriers. Organicmaterials such as walnut-shell flour, cottonseed hulls, wheat flour,wood flour or redwood-bark flour may also be used as solid carriers.

The herbicidal composition will also usually contain a minor amount of asurface-active agent. Such surface agents are those commonly known aswetting agents, dispersing agents and emulsifying agents, and can beanionic, cationic or nonionic in character. The herbicidal compositionsmay also contain other pesticides, adjuvants, stabilizers, conditioners,fillers, and the like.

The amount of herbicidal compound or composition administered will varywith the particular plant part or plant growth medium which is to becontacted, the general location of application--i.e., sheltered areassuch as greenhouses, as compared to exposed areas such as fields--aswell as the desired type of control. Generally, for both pre- andpost-emergent control, the herbicidal compounds of the invention areapplied at rates of 0.2 to 60 kg/ha, and the preferred rate is in therange 0.5 to 40 kg/ha.

Pre-emergent herbicidal tests on representative compounds of theinvention were made using the following method:

Pre-Emergent Test

An acetone solution of the test compound was prepared by mixing 750 mgof the compound, 220 mg of a nonionic surfactant and 25 ml of acetone.This solution was added to approximately 125 ml of water containing 156mg of surfactant.

Seeds of the test vegetation were planted in a pot of soil and the testsolution was sprayed uniformly onto the soil surface at a dose of 33micrograms/cm² (3 lbs/acre). The pot was watered and placed in agreenhouse. The pot was watered intermittently and was observed forseedling emergence, health of emerging seedlings, etc., for a 3-weekperiod. At the end of this period, the herbicidal effectiveness of thecompound was rated based on the physiological observations. A 0-to-100scale was used, 0 representing no phytotoxicity, 100 representingcomplete kill. The results of these tests appear in Table II.

Post-Emergent Test

The test compound was formulated in the same manner as described abovefor the pre-emergent test. The concentration of the test compound inthis formulation was 5000 ppm. This formulation was uniformly sprayed on2 similar pots of 24-day-old plants (approximately 15 to 25 plants perpot) at a dose of 33 mcg/cm² (3 lbs/acre). After the plants had dried,they were placed in a greenhouse and then watered intermittently attheir bases, as needed. The plants were observed periodically forphytotoxic effects and physiological and morphological responses to thetreatment. After 3 weeks, the herbicidal effectiveness of the compoundwas rated based on these observations. A 0-to-100 scale was used, 0representing no phytotoxicity and 100 representing complete kill. Theresults of these tests appear in Table II.

Example 1 Preparation of3-(n-butyl-amino)-1-methylene-2,4-thiazaspiro[5.4]decane

To 1-ethynyl-1-amino-cyclohexane (50 g) in carbon tetrachloride (100 ml)was added dropwise 35 g n-butylthiocyanate. The mixture was stirred atroom temperature for 3 days.

The mixture was stripped of solvent and filtered through a silica gelcolumn in methylene chloride.

The product is reported as Compound 34 in Table I.

Example 2 Preparation of3-(i-propylamino)-1-chloromethylene-2,4-thiazaspiro[5.4]decane

3-(i-Propylamino)-1-methylene-2,4-thiazaspiro [5.4]decane (A) wasprepared as in Example 1 using i-propylthiocyanate.

Chlorine gas (4 g) was dissolved in 100 ml chloroform and added dropwiseto product A (12.65 g). The mixture was stirred at room temperature forone hour, then chromatographed on a silica gel column. Elution by 50%CH₂ Cl₂ /Hexane and by CH₂ Cl₂ yielded two products. The first productrecovered was the dichloro product reported as Compound 59 in Table I.The second product was the title product, reported as Compound 58.

Example 3 Preparation of3-(N-(N'-methylcarbamoyl)-ethylamino)-1-methylene-2,4-thiazaspiro5.4]decane

3-(ethylamino)-1-methylene-2,4-thiazaspiro [5.4]decane (B) was preparedas in Example 1.

Product B (7.2 g) was dissolved in 100 ml benzene and 2.9 g methylisocyanate was added dropwise. A few drops of triethylamine were addedand the mixture was stirred at room temperature for two hours. Themixture was stripped, stirred in hexane, filtered and stripped to yielda yellow oil. The product was crystallized in hexane, mp. 53-57,reported as Compound 39 in Table I.

Example 4 Preparation of3-(sec-butylamino)-1-methylene-2,4-thiazaspiro[5.4]decane

Thiophosgene (140 g) was dissolved in 250 ml methylene chloride and 250ml water was added. To the two-phase system was added dropwise asolution of 1-ethynyl-1-amino-cyclohexane (123 g) and triethylamine (101g) in 250 ml methylene chloride. The mixture was cooled to preventrefluxing. The mixture was stirred at room temperature for two hours,phase separated, and the organic phase was collected. This layer wasdried (MgSO₄) and stripped, and the residue was dissolved in diethylether, filtered and stripped to yield a dark brown oil. A small portionof the oil was purified on a silica gel column (3×10 cm) with hexaneelution to yield 1-isothiocyano-1-ethyl-cyclohexane (A), 5.9 g.

Compound A (10 g) was dissolved in 50 ml methylene chloride andsec-butylamine (4.5 g) was added dropwise. The exotherm caused refluxingand the stirring was continued overnight at room temperature afteraddition of 1.0 g excess sec-butylamine.

The solution was stripped, purified on a silica gel column (3×10 cm)with benzene and hexane elution. The eluates were stripped to yield thetitle product (9.5 g) as a reddish brown oil, reported as Compound 28 inTable I.

                                      TABLE I                                     __________________________________________________________________________    COMPOUNDS OF THE FORMULA                                                       ##STR5##                                                                                                                   Analysis                                                                      S        Cl                     No.                                                                              R.sup.2                                                                             R.sup.3                                                                            R          R.sup.1     X Y m.p., °C.                                                                   Cal. Fd. Cal.                                                                              Fd.                __________________________________________________________________________    1  (CH.sub.2 ).sub.5                                                                        H          CH.sub.2 CH.sub.2 φ                                                                   H H Oil  11.20                                                                              11.5                       1A (CH.sub.2 ).sub.5                                                                        H          CH.sub.2 φ                                                                            H H 56-58                                                                              11.77                                                                              10.9                       2  (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR6##   H H Oil  10.45                                                                              10.7                                                                              11.56                                                                             11.7               3  (CH.sub. 2 ).sub.5                                                                       H                                                                                         ##STR7##   H H 82-84                                                                              10.13                                                                              10.6                       4  (CH.sub.2 ).sub.5                                                                        H          ( CH.sub.2 ).sub.4 φ                                                                  H H Oil  10.20                                                                              11.1                       5  (CH.sub.2 ).sub.5                                                                        CH.sub.3                                                                                  ##STR8##   H H 97-99                                                                              12.66                                                                              12.8                       6  (CH.sub.2 ).sub.5                                                                        (CH.sub.2 ).sub.3 CH.sub.3                                                               CHC(CN).sub.2                                                                             H H Oil  10.20                                                                              10.1                       7  (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR9##   H H Oil  11.60                                                                              12.1                       8  (CH.sub.2 ).sub.5                                                                        H          CH(C.sub.2 H.sub.5).sub.2                                                                 H H Oil  12.70                                                                              13.6                       9  (CH.sub. 2 ).sub.5                                                                       H                                                                                         ##STR10##  H H Oil  12.04                                                                              13.3                       10 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR11##  H H Oil  12.70                                                                              14.5                       11 (CH.sub.2 ).sub.5                                                                        H          CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                      H H Oil  12.70                                                                              13.7                       12 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.4 CH.sub.3                                                                H H Oil  12.70                                                                              13.1                       13 (CH.sub.2 ).sub.5                                                                        H          C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3                                                       H H Oil  12.71                                                                              14.0                       14 (CH.sub.2 ).sub.5                                                                        H          C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3                                              H H Oil  10.89                                                                              11.3                       15 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR12##  H H Oil  12.81                                                                              12.6                       16 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR13##  H H 112-114                                                                            10.13                                                                              10.2                       17 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR14##  H H Oil  11.12                                                                              12.0                       18 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR15##  H H Oil  11.6 11.8                       19 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.11 CH.sub.3                                                               H H Oil   9.15                                                                               8.7                       20 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.5 CH.sub.3                                                                H H Oil  12.01                                                                              12.4                       21 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.7 CH.sub.3                                                                H H Oil  10.89                                                                              11.1                       22 (CH.sub.2 ).sub.5                                                                        CH.sub.2 CH.sub.3                                                                        (CH.sub.2 ).sub.3 CH.sub.3                                                                H H Oil  12.04                                                                              13.2                       23 (CH.sub.2 ).sub.5                                                                        H          CH.sub.2 CH(CH.sub.3).sub.2                                                               H H Oil  13.45                                                                              14.3                       24 (CH.sub.2 ).sub.5                                                                        CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                      H H Oil   9.82                                                                              11.3                       25 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR16##  H H Oil  10.89                                                                              11.9                       26 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR17##  H H 64-67                                                                              12.61                                                                              13.1                       27 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.2 OCH.sub. 3                                                              H H 58-61                                                                              13.34                                                                              14.3                       28 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR18##  H H Oil  13.45                                                                              14.2                       29 (CH.sub.2 ).sub.5                                                                         ##STR19## CH.sub.2 CH.sub.2 CH.sub.3                                                                H H 63-67                                                                              11.39                                                                              11.1                       30 (CH.sub.2 ).sub.5                                                                        (CH.sub.2 ).sub.2 CH.sub.3                                                               (CH.sub.2 ).sub.2 CH.sub.3                                                                H H Oil  12.04                                                                              12.6                       31 (CH.sub.2 ).sub.5                                                                        CH.sub.3   (CH.sub.2 ).sub.3 CH.sub.3                                                                H H Oil  12.71                                                                              12.1                       32 (CH.sub.2 ).sub.5                                                                        H          CH(CH.sub.3).sub.2                                                                        H H Oil  14.30                                                                              13.7                       33 (CH.sub.2 ).sub.5                                                                        H          C(CH.sub.3).sub. 3                                                                        H H 57-58                                                                              13.46                                                                              13.8                       34 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.3 CH.sub.3                                                                H H Oil  13.46                                                                              13.1                       35 (CH.sub.2 ).sub.5                                                                        H          CH.sub.2 CH.sub.2 CH.sub.3                                                                H H Oil  14.29                                                                              14.1                       36 (CH.sub.2 ).sub.5                                                                         ##STR20##                                                                                ##STR21##  H H Oil   9.4  9.2                                                                              10.40                                                                             12.0               37 (CH.sub.2 ).sub.5                                                                         ##STR22## CH.sub.2 CHCH.sub.2                                                                       H H Oil  10.73                                                                              13.8                                                                              11.87                                                                             10.3               38 (CH.sub.2 ).sub.5                                                                        H          CH.sub.2 CHCH.sub.2                                                                       H H Oil  14.4 16.2                       39 (CH.sub.2 ).sub.5                                                                         ##STR23## C.sub.2 H.sub.5                                                                           H H 53-57                                                                              12.0 12.9                       40  (CH.sub.2 ).sub.5                                                                       H          C.sub.2 H.sub.5                                                                           H H Oil  15.25                                                                              14.8                       41 (CH.sub.2 ).sub.5                                                                         ##STR24##                                                                                ##STR25##  H H 81-84                                                                               9.98                                                                              10.2                       42 (CH.sub.2 ).sub.5                                                                        H                                                                                         ##STR26##  H H Oil  12.13                                                                              12.13                      43 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H          C(CH.sub.3).sub.3                                                                         H H Oil  14.17                                                                              14.4                       44 CH.sub.3                                                                            CH.sub.3                                                                           H          (CH.sub.2 ).sub.11 CH.sub.3                                                               H H 54-57                                                                              10.33                                                                               9.8                       45 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H          (CH.sub.2 ).sub.3 CH.sub.3                                                                H H Oil  14.17                                                                              14.7                       46 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H          CH(CH.sub.3).sub.2                                                                        H H Oil  15.10                                                                              15.6                       47 CH.sub.3                                                                            CH.sub.3                                                                           H          (CH.sub.2 ).sub.6  CH.sub.3                                                               H H Oil  13.34                                                                              14.3                       48 CH.sub.3                                                                            CH.sub.3                                                                            ##STR27## CH.sub.3    H H Oil  15.03                                                                              15.8                       49 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                     ##STR28## CH.sub.3    H H Oil  13.29                                                                              14.2                       50 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    CNHCH.sub.3                                                                              C.sub.2 H.sub.5                                                                           H H Oil  14.11                                                                              15.2                       51 CH.sub.3                                                                            CH.sub.3                                                                            ##STR29##                                                                                ##STR30##  H H 67-69                                                                              11.39                                                                              11.6                       52 CH.sub.3                                                                            CH.sub.3                                                                           H                                                                                         ##STR31##  H H 89-93                                                                              14.29                                                                              12.7                       53 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.5 CH.sub.3                                                                Cl                                                                              H Oil  59.87.sup.1                                                                        58.8.sup.1                                                                        9.31.sup.2                                                                        8.9.sup.2                                                                 8.37.sup.3                                                                        8.26.sup.3         54 (CH.sub.2 ).sub.5                                                                        H          ( CH.sub.2 ).sub.5 CH.sub.3                                                               Br                                                                              H Oil  52.16.sup.1                                                                        50.53.sup.1                                                                       8.11.sup.2                                                                        7.53.sup.2                                                                7.30.sup.3                                                                        7.1.sup.3          55 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.5 CH.sub.3                                                                Cl                                                                              Cl                                                                              Oil  53.72.sup.1                                                                        54.11.sup.1                                                                       8.36.sup.2                                                                        7.96.sup.2                                                                7.21.sup.3                                                                        7.55.sup.3         56 (CH.sub.2 ).sub.5                                                                        H          C(CH.sub.3).sub.3                                                                         Cl                                                                              H 104-108                                                                            57.22.sup.1                                                                        57.35.sup.1                                                                       10.27.sup.2                                                                       10.27.sup.2                                                               7.76.sup.3                                                                        7.66.sup.3         57 (CH.sub.2 ).sub.5                                                                        H          C(CH.sub.3).sub.3                                                                         Cl                                                                              Cl                                                                              60-64                                                                              50.81.sup.1                                                                        50.39.sup.1                                                                       9.12.sup.2                                                                        8.92.sup.2                                                                6.56.sup.3                                                                        6.49.sup.3         58 (CH.sub.2 ).sub.5                                                                        H          CH(CH.sub.3).sub.2                                                                        Cl                                                                              H Oil  55.68.sup.1                                                                        51.52.sup.1                                                                       10.83.sup.2                                                                       9.87.sup.2                                                                7.40.sup.3                                                                        6.98.sup.3         59 (CH.sub.2 ).sub.5                                                                        H          CH(CH.sub.3).sub.2                                                                        Cl                                                                              Cl                                                                              --   49.14.sup.1                                                                        52.51.sup.1                                                                       9.55.sup.2                                                                        10.06.sup.2                                                               6.19.sup.3                                                                        6.91.sup.3         60 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.3 CH.sub.3                                                                Cl                                                                              Cl                                                                              Oil  50.81.sup.1                                                                        50.96.sup.1                                                                       9.12.sup.2                                                                        9.34.sup.2                                                                6.56.sup.3                                                                        6.66.sup.3         61 (CH.sub.2 ).sub.5                                                                        H          CH(CH.sub.3).sub.2                                                                        Br                                                                              H Oil  47.52.sup.1                                                                        49.87.sup.1                                                                       9.24.sup.2                                                                        8.74.sup.2                                                                6.31.sup.3                                                                        6.71.sup.3         62 (CH.sub.2 ).sub.5                                                                        H          (CH.sub.2 ).sub.3 CH.sub.3                                                                Br                                                                              H Oil  49.2.sup.                                                                          47.4.sup.1                                                                        8.83.sup.2                                                                        8.48.sup.2                                                                6.67.sup.3                                                                        6.54.sup.3         40A                                                                              (CH.sub.2 ).sub.5                                                                        H          CH.sub.3    H H 77-8 16.34                                                                              16.2                       40B                                                                              (1)         --         --         --                                                                              --                                                                              Oil  15.25                                                                              15.5                       __________________________________________________________________________     ##STR32##                                                                     .sup.1 Carbon                                                                 .sup.2 Nitrogen                                                               .sup.3 Hydrogen                                                          

                  TABLE II                                                        ______________________________________                                        Herbicidal Efficacy                                                           Percent Control-Pre/Post                                                      No.   L       M        P     C      W     O                                   ______________________________________                                         1    0/70    0/100    0/25  0/55   0/30  0/40                                1A    0/80    25/--    0/55  0/65   0/80  0/50                                 2    0/15    0/100    0/0   0/25   0/30  0/25                                 3    0/15    0/35     0/10  0/0    0/0   0/0                                  4    0/75    0/95     0/50  0/55   0/55  0/30                                 5    0/10    0/50     0/10  0/0    0/0   0/0                                  6    0/30    0/100    0/0   0/15   0/10  0/0                                  7    0/50    0/100    0/65  0/15   0/15  0/15                                 8    0/90    0/100    0/60  0/65   0/65  0/65                                 9    65/75   65/75    65/75 0/50   0/60  0/15                                10    0/35    0/50     0/50  0/75   0/80  0/45                                11    0/95    0/100    0/70  0/80   0/80  0/75                                12    0/100   0/100    0/100 0/70   0/75  0/50                                13    0/60    0/85     0/55  0/85   0/85  0/30                                14    0/30    0/100    0/25  0/70   0/60  0/50                                15    0/25    0/50     0/10  0/55   0/60  0/60                                16    0/0     0/100    0/0   0/0    0/0   0/0                                 17    0/20    0/100    0/0   0/0    0/0   0/0                                 18    0/80    0/95     0/60  0/35   0/60  0/40                                19    0/10    0/100    0/25  0/35   0/35  0/35                                20    0/100   0/100    0/85  0/73   0/80  0/80                                21    -/98    0/100    0/60  0/80   0/75  0/60                                22    -/20    0/100    0/0   0/15   0/0   0/0                                 23    -/85    0/98     0/25  0/65   0/75  0/70                                24    -/35    0/98     0/20  0/35   0/0   0/0                                 25    -/92    0/88     0/92  0/72   0/85  0/82                                26    -80     0/-      0/32  0/47   0/55  0/50                                27    -/60    0/-      0/10  0/35   0/25  0/80                                28    -/95    0/-      0/80  0/70   0/55  0/70                                29    0/30    0/-      0/50  0/0    0/0   0/0                                 30    0/25    0/-      0/0   0/43   0/25  0/20                                31    0/0     0/0      0/15  0/40   0/35  0/60                                32    0/100   0/-      0/15  0/96   0/93  0/97                                33    0/30    0/-      0/30  0/99   0/99  0/100                               34    0/100   0/100    0/55  0/55   0/95  0/97                                35    0/70    0/100    0/15  0/30   0/80  0/65                                36    0/0     0/93     0/0   0/0    0/0   0/0                                 37    0/10    0/40     0/0   0/0    0/0   0/0                                 38    0/20    0/85     0/20  0/0    0/0   0/0                                 39    0/95    0/100    0/95  0/50   0/95  0/25                                40    0/25    0/100    0/40  0/30   0/50  0/55                                40A   0/5     0/35     0/0   0/0    0/0   0/0                                 40B   0/85    0/100    0/65  0/40   0/70  0/55                                41    0/25    0/80     0/10  0/0    0/0   0/0                                 42    0/70    0/95     0/25  0/50   0/40  0/25                                43    0/0     0/60     0/0   0/0    0/0   0/0                                 44    0/55    0/85     0/65  0/10   0/20  0/15                                45    0/40    0/100    0/25  0/35   0/35  0/25                                46    0/0     0/85     0/0   0/0    0/0   0/0                                 47    0/90    0/95     0/90  0/30   0/60  0/55                                48    97/40   97/60    77/30 80/0   90/0  95/0                                49    0/25    0/20     0/20  0/0    0/0   0/0                                 50    80/75   93/--    25/70 60/60  90/80 87/97                               51    0/10    0/75     0/10  0/15   0/15  0/15                                52    0/10    0/75     0/0   0/0    0/0   0/0                                 53    0/40    0/100    0/0   0/10   0/60  0/55                                54    0/37    0/85     0/25  0/10   0/37  0/0                                 55    0/20    0/45     0/0   0/0    0/0   0/0                                 56    0/15    0/100    0/10  0/0    0/27  0/35                                57    0/20    0/50     0/0   0/0    0/0   0/0                                 58    0/65    0/100    0/60  0/30   0/60  0/00                                59    0/20    0/100    0/15  0/10   0/50  0/35                                60    0/30    0/90     0/30  0/10   0/35  0/35                                61    0/55    0/97     0/35  0/15   0/40  0/45                                62    0/80    0/95     0/30  0/25   0/55  0/10                                ______________________________________                                         O = Wild Oats (Avena fatua)                                                   W = Watergrass (Echinochloa crusgalli)                                        C = Crabgrass (Digitaria Sanguinalis)                                         M = Mustard (Brassica arvensis)                                               P = Pigweed (Amaranthus retroflexus)                                          L = Lambsquarter (Chenopodium album)                                     

What is claimed is:
 1. A compound of the formula ##STR33## wherein X andY are individually hydrogen or halogen; R² and R³ are individually alkylof 1 to 3 carbon atoms or R² and R³ are joined to form a cycloalkylgroup of 3 to 8 carbon atoms;R is hydrogen, alkyl of 1 to 4 carbon atomsor alkoxyalkyl of 2 to 20 carbon atoms; and R¹ is alkyl of 1 to 20carbon atoms, alkenyl or alkynyl of 3 to 20 carbon atoms, cycloalkyl orpolycycloalkyl of 5 to 12 carbon atoms, alkoxyalkyl of 2 to 20 carbonatoms, cyanoalkyl or cyanoalkenyl of 3 to 20 carbon atoms; with theproviso that when R and R¹ are both alkyl groups as defined above, R andR¹ each contain at least 3 carbon atoms.
 2. A compound according toclaim 1 wherein R² and R³ are joined to form a cyclopentyl, cyclohexylor cycloheptyl ring.
 3. A compound according to claim 2 wherein R² andR³ form a cyclohexyl ring.
 4. A compound according to claim 3 wherein Xand Y are hydrogen.
 5. A compound according to claim 4 wherein R¹ isalkyl of 2 to 20 carbon atoms.
 6. The compound according to claim 5wherein R is hydrogen and R¹ is iso-butyl.
 7. An herbicidal compositioncomprising a biologically inert carrier and an herbicidally effectiveamount of a compound of the formula defined in claim 1.